# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_238EXT_0m_d_b
_database_code_depnum_ccdc_archive 'CCDC 1532657'
_audit_update_record             
;
2017-02-14 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Cu N2 O5'
_chemical_formula_weight         505.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4915(2)
_cell_length_b                   17.4030(5)
_cell_length_c                   24.2402(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2316.60(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      28.19

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.983
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_T_max  0.789
_exptl_absorpt_process_details   'APEX2 (Bruker AXS Inc. 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Mo
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20140
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5726
_reflns_number_gt                5126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+1.4295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.072(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5726
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3537(9) 0.3280(3) 0.84938(18) 0.0444(10) Uani 1 1 d . . . . .
H1 H 0.2452 0.2972 0.8299 0.053 Uiso 1 1 calc R U . . .
Cu1 Cu 0.50034(10) 0.37378(2) 0.73690(2) 0.02348(11) Uani 1 1 d . . . . .
N1 N 0.5138(7) 0.37064(16) 0.82105(11) 0.0332(6) Uani 1 1 d . . . . .
O1 O 0.4886(6) 0.48377(12) 0.73956(11) 0.0345(5) Uani 1 1 d . . . . .
C2 C 0.3433(9) 0.3278(3) 0.90603(19) 0.0486(11) Uani 1 1 d . . . . .
H2 H 0.2277 0.2976 0.9238 0.058 Uiso 1 1 calc R U . . .
N2 N 0.5342(6) 0.37718(16) 0.65316(12) 0.0316(7) Uani 1 1 d . . . . .
O2 O 0.8798(6) 0.51009(15) 0.7307(2) 0.0597(10) Uani 1 1 d . . . . .
C3 C 0.5020(9) 0.3719(2) 0.93703(14) 0.0392(7) Uani 1 1 d . . . . .
O3 O 0.0999(5) 0.37178(16) 0.73070(16) 0.0444(7) Uani 1 1 d . . . . .
C4 C 0.6701(10) 0.4153(3) 0.90712(19) 0.0543(12) Uani 1 1 d . . . . .
H4 H 0.7827 0.4458 0.9256 0.065 Uiso 1 1 calc R U . . .
O4 O 0.4920(6) 0.76324(11) 0.76575(10) 0.0319(5) Uani 1 1 d . . . . .
C5 C 0.6698(9) 0.4132(3) 0.85029(18) 0.0473(11) Uani 1 1 d . . . . .
H5 H 0.7835 0.4428 0.8314 0.057 Uiso 1 1 calc R U . . .
O5 O 0.1183(5) 0.74369(15) 0.73258(18) 0.0554(9) Uani 1 1 d . . . . .
C6 C 0.4946(9) 0.3740(2) 0.99841(15) 0.0445(8) Uani 1 1 d . . . . .
C7 C 0.3336(16) 0.3328(5) 1.0278(2) 0.110(3) Uani 1 1 d . . . . .
H7 H 0.2230 0.3015 1.0094 0.132 Uiso 1 1 calc R U . . .
C8 C 0.3279(18) 0.3355(6) 1.0846(3) 0.121(4) Uani 1 1 d . . . . .
H8 H 0.2104 0.3072 1.1033 0.145 Uiso 1 1 calc R U . . .
C9 C 0.4838(13) 0.3771(4) 1.11352(19) 0.0695(14) Uani 1 1 d . . . . .
H9 H 0.4810 0.3772 1.1519 0.083 Uiso 1 1 calc R U . . .
C10 C 0.6442(17) 0.4187(6) 1.0857(3) 0.123(4) Uani 1 1 d . . . . .
H10 H 0.7524 0.4498 1.1050 0.148 Uiso 1 1 calc R U . . .
C11 C 0.6551(15) 0.4170(5) 1.0284(3) 0.108(3) Uani 1 1 d . . . . .
H11 H 0.7734 0.4457 1.0102 0.130 Uiso 1 1 calc R U . . .
C12 C 0.6886(9) 0.3340(3) 0.62457(19) 0.0483(11) Uani 1 1 d . . . . .
H12 H 0.7986 0.3035 0.6438 0.058 Uiso 1 1 calc R U . . .
C13 C 0.6931(10) 0.3324(3) 0.5680(2) 0.0542(12) Uani 1 1 d . . . . .
H13 H 0.8048 0.3010 0.5500 0.065 Uiso 1 1 calc R U . . .
C14 C 0.5326(8) 0.3771(2) 0.53721(16) 0.0399(9) Uani 1 1 d . . . . .
C15 C 0.3757(10) 0.4225(3) 0.5680(2) 0.0539(12) Uani 1 1 d . . . . .
H15 H 0.2646 0.4540 0.5499 0.065 Uiso 1 1 calc R U . . .
C16 C 0.3812(10) 0.4217(3) 0.62452(19) 0.0471(11) Uani 1 1 d . . . . .
H16 H 0.2744 0.4534 0.6437 0.056 Uiso 1 1 calc R U . . .
C17 C 0.5291(9) 0.3762(3) 0.47546(17) 0.0469(10) Uani 1 1 d . . . . .
C18 C 0.6976(14) 0.3349(5) 0.4459(3) 0.082(2) Uani 1 1 d . . . . .
H18 H 0.8168 0.3070 0.4644 0.099 Uiso 1 1 calc R U . . .
C19 C 0.6907(16) 0.3346(6) 0.3882(3) 0.102(3) Uani 1 1 d . . . . .
H19 H 0.8057 0.3064 0.3686 0.122 Uiso 1 1 calc R U . . .
C20 C 0.5182(13) 0.3749(4) 0.3605(2) 0.082(2) Uani 1 1 d . . . . .
H20 H 0.5146 0.3746 0.3222 0.099 Uiso 1 1 calc R U . . .
C21 C 0.3528(15) 0.4153(6) 0.3892(3) 0.102(3) Uani 1 1 d . . . . .
H21 H 0.2347 0.4432 0.3703 0.122 Uiso 1 1 calc R U . . .
C22 C 0.3547(13) 0.4163(5) 0.4465(2) 0.086(2) Uani 1 1 d . . . . .
H22 H 0.2372 0.4443 0.4654 0.103 Uiso 1 1 calc R U . . .
C23 C 0.6657(6) 0.52892(17) 0.73497(16) 0.0264(6) Uani 1 1 d . . . . .
C24 C 0.6078(7) 0.61289(17) 0.73859(16) 0.0266(7) Uani 1 1 d . . . . .
H24 H 0.7347 0.6483 0.7384 0.032 Uiso 1 1 calc R U . . .
C25 C 0.3817(7) 0.63792(17) 0.74197(15) 0.0254(7) Uani 1 1 d . . . . .
H25 H 0.2552 0.6024 0.7412 0.030 Uiso 1 1 calc R U . . .
C26 C 0.3213(7) 0.72136(18) 0.74700(13) 0.0248(7) Uani 1 1 d . . . . .
H3A H 0.025(9) 0.409(3) 0.7400(17) 0.036(11) Uiso 1 1 d . . . . .
H3B H 0.048(11) 0.331(3) 0.739(2) 0.063(16) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.340(5) . ?
C1 C2 1.374(6) . ?
C1 H1 0.9300 . ?
Cu1 O1 1.916(2) . ?
Cu1 O4 1.9254(19) 3_646 ?
Cu1 N2 2.039(3) . ?
Cu1 N1 2.042(3) . ?
Cu1 O3 2.204(3) . ?
N1 C5 1.336(5) . ?
O1 C23 1.255(4) . ?
C2 C3 1.384(6) . ?
C2 H2 0.9300 . ?
N2 C12 1.328(5) . ?
N2 C16 1.337(5) . ?
O2 C23 1.225(4) . ?
C3 C4 1.396(6) . ?
C3 C6 1.489(5) . ?
O3 H3A 0.80(5) . ?
O3 H3B 0.79(6) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
O4 C26 1.271(5) . ?
O4 Cu1 1.9254(19) 3_656 ?
C5 H5 0.9300 . ?
O5 C26 1.232(5) . ?
C6 C7 1.344(7) . ?
C6 C11 1.365(8) . ?
C7 C8 1.378(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.322(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.324(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.392(9) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.371(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(6) . ?
C14 C17 1.497(5) . ?
C15 C16 1.371(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.373(8) . ?
C17 C22 1.378(8) . ?
C18 C19 1.399(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.357(10) . ?
C19 H19 0.9300 . ?
C20 C21 1.343(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.388(8) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.498(4) . ?
C24 C25 1.319(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.494(4) . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.7(4) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
O1 Cu1 O4 179.32(13) . 3_646 ?
O1 Cu1 N2 90.43(12) . . ?
O4 Cu1 N2 89.64(11) 3_646 . ?
O1 Cu1 N1 89.68(12) . . ?
O4 Cu1 N1 90.33(11) 3_646 . ?
N2 Cu1 N1 172.68(15) . . ?
O1 Cu1 O3 89.11(12) . . ?
O4 Cu1 O3 90.21(12) 3_646 . ?
N2 Cu1 O3 91.35(14) . . ?
N1 Cu1 O3 95.97(15) . . ?
C5 N1 C1 117.1(3) . . ?
C5 N1 Cu1 122.6(3) . . ?
C1 N1 Cu1 120.2(3) . . ?
C23 O1 Cu1 126.6(2) . . ?
C1 C2 C3 121.0(4) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C12 N2 C16 117.3(4) . . ?
C12 N2 Cu1 124.1(3) . . ?
C16 N2 Cu1 118.4(3) . . ?
C2 C3 C4 115.8(4) . . ?
C2 C3 C6 122.6(4) . . ?
C4 C3 C6 121.6(4) . . ?
Cu1 O3 H3A 118(4) . . ?
Cu1 O3 H3B 111(4) . . ?
H3A O3 H3B 119(5) . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C26 O4 Cu1 125.2(2) . 3_656 ?
N1 C5 C4 123.1(4) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C7 C6 C11 115.8(5) . . ?
C7 C6 C3 122.4(5) . . ?
C11 C6 C3 121.8(5) . . ?
C6 C7 C8 121.8(6) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 H7 119.1 . . ?
C9 C8 C7 122.3(6) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 117.4(5) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
C9 C10 C11 121.7(6) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C6 C11 C10 121.0(6) . . ?
C6 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
N2 C12 C13 123.0(4) . . ?
N2 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 115.0(4) . . ?
C15 C14 C17 122.5(4) . . ?
C13 C14 C17 122.5(4) . . ?
C16 C15 C14 121.3(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
N2 C16 C15 122.6(4) . . ?
N2 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
C18 C17 C22 117.9(5) . . ?
C18 C17 C14 121.2(5) . . ?
C22 C17 C14 120.9(5) . . ?
C17 C18 C19 120.3(7) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.8(7) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.2(5) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 121.2(7) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C17 C22 C21 120.6(7) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
O2 C23 O1 125.7(3) . . ?
O2 C23 C24 118.0(3) . . ?
O1 C23 C24 116.2(3) . . ?
C25 C24 C23 121.7(3) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 122.3(3) . . ?
C24 C25 H25 118.8 . . ?
C26 C25 H25 118.8 . . ?
O5 C26 O4 126.0(3) . . ?
O5 C26 C25 119.0(3) . . ?
O4 C26 C25 115.0(3) . . ?

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.058

